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Creepiest Ghost Stories From Chicago

Updated September 23, 2021 15.1k votes 3.2k voters 194k views13 items

List RulesVote up the Windy City ghost story that freaks you out the most.

Chicago is a city with its own fair share of tragedy and pain. Natural disasters, horrible accidents, and bloody mass slayings are deeply ingrained in the city's culture and past, creating a series of terrifying urban legends and ghost stories. The ghost stories about Chicago are some of the creepiest in the United States, but they also highlight just how much the city has been through since it was formed. Below, you'll find a list of some of the most haunted places in Chicago and a few Chicago ghosts you never want to run into.

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  • 5

    The Eastland Disaster

    Photo: Chicago Daily News photographer / Wikimedia Commons / Public Domain

    The capsizing of the Eastland steamer in Chicago is one of the worst boating disasters of all time. As the gigantic ship made its way toward Michigan City, a horrible event caused the ship to tip over. Out of the estimated 2,500 people who were on board, the casualty tally reached nearly 850. The mystery of why exactly the boat tipped over was never solved. But the story was far from over .

    The armory building where most of the departed were taken during the disaster eventually was taken over by Oprah Winfrey and her studio. A lot of the crew who worked on the show claimed that the ghosts of the passengers often haunted the building. They heard strange noises, like children's laughter and the clinking of phantom glasses, and even saw apparitions, the most popular being one they dubbed the Gray Lady . Even the site of the actual disaster is supposedly haunted, with reports of people passing by the spot hearing the bloodcurdling screams of the doomed passengers.

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  • 6

    The Fort Dearborn Massacre

    America is built on bloody fights and skirmishes, and the Fort Dearborn Massacre still stands as one of the bloodiest. As a result of the War of 1812, tensions between settlers and Native Americans were running hot. Fort Dearborn was a stronghold, but its commander, Captain Nathan Heald, was advised to evacuate and leave everything to the Native Americans. Heald didn't react in time, and soon the whole fort was surrounded by Potawatomi Indians. After tense negotiations and broken promises by each side, a bloody fight took place, taking the lives of more than 50 people. 

    With that much carnage, it's no wonder that ghostly tales started to emerge. Soon, it was said that the site of the fort itself was haunted, but reports calmed down once the fort was torn down and the city of Chicago was built over it. Then in the early 1980s, construction was done in the area and human remains were found and were dated back to the event. Weeks later, people began to see semi-transparent figures in pioneer clothing and military uniforms. Most of them were reported to look very frightened or were screaming in silence. 

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  • 7

    The Grimes Sisters

    Photo: user uploaded image

    The mysterious disappearance of sisters Patricia and Barbara Grimes in 1956 shook Chicago to its core. The massive manhunt to find these girls took some wild turns , but tragically ended with their cadavers being found in the woods. The search to find out who slew them took a massive toll on the public and the police, and their cases still remain unsolved. Even though police supposedly questioned thousands of people over the course of the investigation, they never could find the evidence that they needed.

    Sadly, the girls' cadavers were dumped at the edge of a ravine just a few feet from the shoulder of the road. Near the spot where they were found, a small house was nestled among the trees. The family who lived there mysteriously abandoned the house not long after, and eventually, vandals burned the house down. Some believe the family left the house because it was haunted by the ghosts of the Grimes sisters, and the many reports of strange happenings that trickle in from people who explore the area around the house seem to confirm that theory.

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  • 8

    The St. Valentine's Day Massacre

    Photo: ryochiji / flickr / CC-BY 2.0

    Anybody who has taken a history class has at least heard of the St. Valentine's Day Massacre . It was a bloody onslaught that both wiped out any opposition to Al Capone's empire and was also the start of his downfall, as it convinced the public that Capone needed to be stopped. Seven people lost their lives in a vicious execution on Clark Street and their spirits supposedly still haunt the spot to this very day.

    People claim to hear screams and machine-gun fire as they pass the site of the mass slaying, and can't help feeling immense fear when they are in the area. It also affects pets, who bark or whine when they walk by the place.

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